methyl 5-deoxy-2,3-O-isopropylidene-5-C--β-D-ribofuranoside

Base Information

• Chemical Name: methyl 5-deoxy-2,3-O-isopropylidene-5-C--β-D-ribofuranoside
• CAS No.: 102997-74-0
• Molecular Formula: C₁₆H₂₃O₆P
• Molecular Weight: 342.329

Synonyms:methyl 5-deoxy-2,3-O-isopropylidene-5-C--β-D-ribofuranoside

Chemical Property of methyl 5-deoxy-2,3-O-isopropylidene-5-C--β-D-ribofuranoside

Chemical Property:

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Technology Process of methyl 5-deoxy-2,3-O-isopropylidene-5-C--β-D-ribofuranoside

There total 4 articles about methyl 5-deoxy-2,3-O-isopropylidene-5-C--β-D-ribofuranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

methyl 5-O--2,3-O-isopropylidene-5-C--β-D-allo- and α-L-talo-pentofuranoside (102997-73-9) → methyl 5-deoxy-2,3-O-isopropylidene-5-C--β-D-ribofuranoside (102997-74-0)

Guidance literature:

With tri-n-butyl-tin hydride; In toluene; at 120 ℃; for 1h;

DOI:10.1016/0008-6215(86)80051-9

Reference yield:

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde (33985-40-9) → methyl 5-deoxy-2,3-O-isopropylidene-5-C--β-D-ribofuranoside (102997-74-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / 20 °C

2: toluene / Heating

3: n-Bu₃SnH / toluene / Heating

With tri-n-butyl-tin hydride; triethylamine; In toluene;

Reference yield:

methyl phenylphosphinate (7162-15-4,111469-75-1,121467-78-5) → methyl 5-deoxy-2,3-O-isopropylidene-5-C--β-D-ribofuranoside (102997-74-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / 20 °C

2: toluene / Heating

3: n-Bu₃SnH / toluene / Heating

With tri-n-butyl-tin hydride; triethylamine; In toluene;

upstream raw materials:

methyl 5-O--2,3-O-isopropylidene-5-C--β-D-allo- and α-L-talo-pentofuranoside

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

methyl phenylphosphinate

methyl 2,3-O-isopropylidene-5-C--β-D-allo- and α-L-talo-pentofuranoside

Downstream raw materials:

(3R,4R,5S)-1-Oxo-1-phenyl-1λ⁵-phosphinane-2,3,4,5-tetraol

1,2,3,4-tetra-O-acetyl-5-deoxy-5-C-<(R)-phenylhosphinyl>-α-D-ribopyranose

1,2,3,4-tetra-O-acetyl-5-deoxy-5-C-<(R)-phenylhosphinyl>-β-D-ribopyranose

1,2,3,4-tetra-O-acetyl-5-deoxy-5-C-<(S)-phenylphosphinyl>-α-D-ribopyranose

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